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$53+ Cheap flights from Chesapeake, VA to Massachusetts

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BOS
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Cheap flight deals from Chesapeake to Massachusetts

Keep the following information in mind while searching for Chesapeake to Massachusetts flight deals. Data was last updated November 6, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$102
(Kiwi.com)

One-way from

$53
(Kiwi.com)

Popular in

November

Cheapest in

July

Average price

$386
Provider with most accurate pricing for Norfolk-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Boston Logan Intl flights.
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From Chesapeake to Massachusetts
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One-way flight from Chesapeake to Massachusetts
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Highest demand for flights based on searches. 18% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Chesapeake to Massachusetts

Cheapest flights from Chesapeake to Massachusetts
Explore the most affordable flight options available from Chesapeake to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/129:25 pmORF - BDL
Nonstop1h 27mBreeze Airways
Sun 12/147:10 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 11/5$102
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/208:51 pmORF - BDL
Nonstop1h 27mBreeze Airways
Sun 11/237:10 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 11/6$108
This Breeze Airways deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:51 pmORF - BDL
Nonstop1h 27mBreeze Airways
Thu 12/187:10 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 11/5$113
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/208:51 pmORF - BDL
Nonstop1h 27mBreeze Airways
Mon 11/247:10 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 11/4$122
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/208:51 pmORF - BDL
Nonstop1h 27mMultiple Airlines
Sun 11/238:27 pmBDL - ORF
1 stop13h 16mMultiple Airlines
Deal found 11/6$141
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:38 amORF - BOS
1 stop25h 23mMultiple Airlines
Sat 1/1011:47 amBOS - ORF
1 stop24h 28mMultiple Airlines
Deal found 11/4$143
This Mytrip deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/39:26 pmORF - BOS
1 stop12h 37mSpirit Airlines
Wed 12/108:11 pmBOS - ORF
1 stop11h 32mSpirit Airlines
Deal found 11/5$153
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:38 amORF - BOS
1 stop25h 23mMultiple Airlines
Sun 1/116:00 amBOS - ORF
1 stop28h 51mMultiple Airlines
Deal found 11/4$163
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:38 amORF - BDL
2 stops14h 05mMultiple Airlines
Sun 12/147:10 amBDL - ORF
Nonstop1h 37mMultiple Airlines
Deal found 11/5$166
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:38 amORF - BOS
1 stop25h 23mSpirit Airlines
Sun 12/78:11 pmBOS - ORF
1 stop11h 32mSpirit Airlines
Deal found 11/5$167
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/209:26 pmORF - BDL
1 stop19h 51mMultiple Airlines
Mon 11/247:10 amBDL - ORF
Nonstop1h 37mMultiple Airlines
Deal found 11/4$176
This Cheapflightsfares deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:38 amORF - BOS
1 stop10h 28mSpirit Airlines
Sun 1/113:43 pmBOS - ORF
1 stop6h 05mSpirit Airlines
Deal found 11/6$185

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 6, 2025.
Use the filters below to find and compare flights from Chesapeake to Massachusetts that are best for you.

Fly from

Chesapeake

Fly to

Massachusetts

Route

Depart

Return

Price

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Fri 12/12

9:25 pm-10:52 pm

Nonstop1h 27m

Hartford Bradley Intl

Sun 12/14

7:10 am-8:47 am

Nonstop1h 37m

$102

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Fri 2/6

9:18 pm-10:45 pm

Nonstop1h 27m

Hartford Bradley Intl

Sun 2/8

7:10 am-8:48 am

Nonstop1h 38m

$108

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 11/20

8:51 pm-10:18 pm

Nonstop1h 27m

Hartford Bradley Intl

Mon 11/24

7:10 am-8:47 am

Nonstop1h 37m

$122

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 11/20

8:51 pm-10:18 pm

Nonstop1h 27m

Hartford Bradley Intl

Sun 11/23

8:27 pm-9:43 am

1 stop13h 16m

$141

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Wed 1/7

7:40 pm-10:11 am

1 stop14h 31m

Boston Logan Intl

Fri 1/9

10:07 am-1:26 pm

1 stop27h 19m

$160

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Fri 12/12

8:38 am-10:43 pm

2 stops14h 05m

Hartford Bradley Intl

Sun 12/14

7:10 am-8:47 am

Nonstop1h 37m

$166

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Fri 5/1

8:15 pm-9:56 pm

Nonstop1h 41m

Boston Logan Intl

Mon 5/4

5:30 pm-7:20 pm

Nonstop1h 50m

$197

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 11/20

1:09 pm-5:17 pm

2 stops28h 08m

Hartford Bradley Intl

Mon 11/24

7:10 am-8:47 am

Nonstop1h 37m

$197

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Thu 12/4

12:27 pm-2:10 pm

Nonstop1h 43m

Boston Logan Intl

Mon 12/8

9:48 am-11:47 am

Nonstop1h 59m

$199

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Fri 1/9

9:18 pm-10:45 pm

Nonstop1h 27m

Hartford Bradley Intl

Sat 1/17

8:19 pm-12:18 pm

1 stop15h 59m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 59 results
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Best time to book a flight from Chesapeake to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Chesapeake with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chesapeake to Massachusetts

What is the cheapest month to book a flight from Chesapeake to Massachusetts?

Currently, July is the cheapest month in which you can book a flight from Chesapeake to Massachusetts (average of $50). Flying from Chesapeake to Massachusetts in March is currently the most expensive (average of $104). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from C6E to MA?

Find hourly flight availability from Chesapeake to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 6, 2025.

It’s optimal to fly from Chesapeake to Massachusetts in the afternoon. By choosing this option you can save up to 39% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Chesapeake to Massachusetts?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Massachusetts. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chesapeake to Massachusetts flight should consider departing on Friday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chesapeake to Massachusetts

Explore weekly flight availability from Chesapeake to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 6, 2025.

The most flights from C6E to USMA are scheduled on a Thursday (31 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (12 on average).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated November 6, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Chesapeake to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,001 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,001 reviews
Delta
7.9
Good
8,001 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,003 reviews
Delta
7.9
Good
8,001 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,040 reviews
Delta
7.9
Good
8,001 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,907 reviews
Delta
7.9
Good
8,001 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Allegiant Air
7.2
Good
697 reviews
Delta
7.9
Good
8,001 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How popular is this Chesapeake to Massachusetts flight route?

    Within the past month, 13 users have taken a look at flights from Chesapeake to Massachusetts.

  • How long is the flight from Chesapeake to Massachusetts?

    Airlines like Breeze Airways, JetBlue, and Delta fly from Chesapeake to Massachusetts in about 1h 27m. The time it takes to get you to your destination is usually consistent. The distance between Chesapeake and Massachusetts is about 395 mi. Generally, flights for this route are nonstop.

  • What are the cheapest airlines to fly from Chesapeake to Massachusetts one-way?

    For one-way options, check prices for Breeze Airways. According to our data, you can fly for as low as $74. Users have also found prices from $93 and $101 on Spirit Airlines and Delta, respectively.

  • What are the most popular routes from Chesapeake to Massachusetts?

    When deciding which route to take from Chesapeake to Massachusetts consider Norfolk - Boston Logan Intl, Norfolk - Albany Intl or Norfolk - Hartford Bradley Intl as they are the most popular.

  • What are the most reliable airlines from Chesapeake to Massachusetts?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chesapeake to Massachusetts on time: Japan Airlines (92%), Etihad Airways (88%), Scandinavian Airlines (85%).

  • What are the cheapest flights from Chesapeake to Massachusetts?

    The cheapest flight price from Chesapeake to Massachusetts is $68. On average you can expect to pay $242. The most popular route, (Norfolk - Boston Logan Intl), can usually be booked for $170.

  • Can I find deals for flights from Chesapeake to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Massachusetts.

  • Can I find deals for business class flights from Chesapeake to Massachusetts?

    Yes. Cheapflights offers flight deals from Chesapeake to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chesapeake to Massachusetts?

    Currently, July is the cheapest month in which you can book a flight from Chesapeake to Massachusetts (average of $50). Flying from Chesapeake to Massachusetts in March is currently the most expensive (average of $104). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top 8 airlines flying from Chesapeake to Massachusetts

Discover the top 8 airlines that operate flights from Chesapeake to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$48Average$90FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$82Average$142FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$85Average$176FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$93Average$248FlexibilityNo cancel feeOn-time62%
DeltaCheapest$95Average$283FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$154Average$324FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$156Average$317FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$166Average$370FlexibilityNo cancel feeOn-time63%

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